NPASS Compound

Natural Product: NPC158285

Natural Product ID	NPC158285
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	RUVPNJSJTWTANE-LFCBYZEKSA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	301751
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000258] Steroids and steroid derivatives [CHEMONTID:0001125] Steroid lactones [CHEMONTID:0001560] Withanolides and derivatives

The Chemical Classification was calculated by Classyfire, a software for chemical taxonomy calculation. Reference: DOI:10.1186/s13321-016-0174-y.

Chemical Representations

RDKit 3D 73 78 0 0 0 0 0 0 0 0999 V2000 6.5000 1.4783 -1.3377 C 0 0 0 0 0 0 0 0 0 0 0 0 5.7340 0.7546 -0.2274 C 0 0 0 0 0 0 0 0 0 0 0 0 6.4034 0.1437 0.7187 C 0 0 0 0 0 0 0 0 0 0 0 0 7.8986 0.2072 0.6340 C 0 0 0 0 0 0 0 0 0 0 0 0 5.7351 -0.5705 1.7884 C 0 0 0 0 0 0 0 0 0 0 0 0 6.3857 -1.1507 2.6898 O 0 0 0 0 0 0 0 0 0 0 0 0 4.3382 -0.5632 1.7394 O 0 0 0 0 0 0 0 0 0 0 0 0 3.6984 -0.3943 0.4439 C 0 0 2 0 0 0 0 0 0 0 0 0 4.2558 0.7734 -0.2413 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2209 -0.3347 0.8202 C 0 0 1 0 0 0 0 0 0 0 0 0 2.0878 0.7081 1.8627 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2923 -0.3304 -0.3195 C 0 0 2 0 0 0 0 0 0 0 0 0 1.2928 0.8813 -1.2010 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1396 1.1649 -1.6195 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9077 0.6264 -0.4970 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.2981 0.1517 -0.8239 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.0612 1.3770 -1.3470 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.4556 0.9191 -1.6123 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.0425 -0.0716 -0.8127 C 0 0 2 0 0 0 0 0 0 0 0 0 -6.5565 -0.0311 -0.6174 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.8754 0.8952 0.4834 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.1211 0.7985 1.5717 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0565 -0.1931 1.6003 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.7537 -0.6889 2.7202 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.3222 -0.6349 0.3605 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.4897 -2.1450 0.3164 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9106 -0.1869 0.5154 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.1061 -1.0907 1.3515 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6101 -0.9309 1.2858 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1259 -0.6258 -0.0729 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.6309 -1.7735 -0.9678 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.5847 -0.4585 -2.0852 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.0560 1.5360 0.5367 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7619 -1.3907 -1.1525 O 0 0 0 0 0 0 0 0 0 0 0 0 2.0703 -1.5938 1.4615 O 0 0 0 0 0 0 0 0 0 0 0 0 7.0913 2.2741 -0.8849 H 0 0 0 0 0 0 0 0 0 0 0 0 5.7818 1.8023 -2.0929 H 0 0 0 0 0 0 0 0 0 0 0 0 7.1801 0.7380 -1.8137 H 0 0 0 0 0 0 0 0 0 0 0 0 8.2907 -0.1813 1.5865 H 0 0 0 0 0 0 0 0 0 0 0 0 8.2173 1.2792 0.4948 H 0 0 0 0 0 0 0 0 0 0 0 0 8.2882 -0.3480 -0.2382 H 0 0 0 0 0 0 0 0 0 0 0 0 3.9629 -1.3147 -0.1106 H 0 0 0 0 0 0 0 0 0 0 0 0 3.9843 0.7091 -1.3254 H 0 0 0 0 0 0 0 0 0 0 0 0 3.9683 1.7531 0.1944 H 0 0 0 0 0 0 0 0 0 0 0 0 3.0798 1.2135 2.0979 H 0 0 0 0 0 0 0 0 0 0 0 0 1.8090 0.2914 2.8785 H 0 0 0 0 0 0 0 0 0 0 0 0 1.4106 1.5352 1.6753 H 0 0 0 0 0 0 0 0 0 0 0 0 1.7691 1.7692 -0.7460 H 0 0 0 0 0 0 0 0 0 0 0 0 1.8004 0.7286 -2.1789 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.3951 0.7365 -2.6103 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.3048 2.2812 -1.6653 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.3750 -0.6168 -1.5807 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.5731 1.7749 -2.2592 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.0936 2.1128 -0.5169 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.0774 1.6516 -2.1653 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.9647 0.4047 -1.5770 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.0174 -1.0100 -0.5217 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.6616 1.6112 0.4338 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.3308 1.4648 2.3965 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.9062 -2.6356 -0.4687 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.4113 -2.6122 1.3201 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.5675 -2.3223 0.0242 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.9491 0.8098 1.0547 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.3816 -0.8822 2.4309 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.4411 -2.1366 1.2015 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.2271 -1.8746 1.7332 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.3456 -0.0557 1.9505 H 0 0 0 0 0 0 0 0 0 0 0 0 0.1494 -2.5818 -0.8413 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.5616 -2.2114 -0.6136 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.5964 -1.5037 -2.0297 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.0682 2.4489 0.1041 H 0 0 0 0 0 0 0 0 0 0 0 0 2.1258 -2.1319 -0.6490 H 0 0 0 0 0 0 0 0 0 0 0 0 2.7694 -2.2277 1.2674 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 2 3 2 0 3 4 1 0 3 5 1 0 5 6 2 0 5 7 1 0 7 8 1 0 8 9 1 0 8 10 1 0 10 11 1 0 10 12 1 0 12 13 1 0 13 14 1 0 14 15 1 0 15 16 1 0 16 17 1 0 17 18 1 0 18 19 1 0 19 20 1 0 20 21 1 0 21 22 2 0 22 23 1 0 23 24 2 0 23 25 1 0 25 26 1 6 25 27 1 0 27 28 1 0 28 29 1 0 29 30 1 0 30 31 1 6 19 32 1 6 15 33 1 1 12 34 1 6 10 35 1 1 9 2 1 0 30 12 1 0 30 15 1 0 27 16 1 0 32 18 1 0 25 19 1 0 1 36 1 0 1 37 1 0 1 38 1 0 4 39 1 0 4 40 1 0 4 41 1 0 8 42 1 6 9 43 1 0 9 44 1 0 11 45 1 0 11 46 1 0 11 47 1 0 13 48 1 0 13 49 1 0 14 50 1 0 14 51 1 0 16 52 1 6 17 53 1 0 17 54 1 0 18 55 1 6 20 56 1 0 20 57 1 0 21 58 1 0 22 59 1 0 26 60 1 0 26 61 1 0 26 62 1 0 27 63 1 1 28 64 1 0 28 65 1 0 29 66 1 0 29 67 1 0 31 68 1 0 31 69 1 0 31 70 1 0 33 71 1 0 34 72 1 0 35 73 1 0 M END

Standard InCHIKey	RUVPNJSJTWTANE-LFCBYZEKSA-N
Standard InCHI	InChI=1S/C28H38O7/c1-15-13-20(34-22(30)16(15)2)25(5,31)28(33)12-11-26(32)18-14-21-27(35-21)9-6-7-19(29)24(27,4)17(18)8-10-23(26,28)3/h6-7,17-18,20-21,31-33H,8-14H2,1-5H3/t17-,18+,20+,21+,23-,24-,25-,26+,27+,28-/m0/s1
SMILES	CC1=C(C)C(=O)O[C@H](C1)[C@@](C)([C@@]1(CC[C@]2([C@@H]3C[C@@H]4[C@@]5(CC=CC(=O)[C@]5(C)[C@H]3CC[C@]12C)O4)O)O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	486.26	Volume:	492.491 ? Van der Waals volume.
Dense:	0.987	LogP:	1.598 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	2.115 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-3.734 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	2.0	Rigid Bonds:	30.0
TPSA:	116.59 ? Topological Polar Surface Area.	H-Bond Acceptor:	7.0
H-Bond Donor:	3.0	Rings:	6.0
Heavy Atoms:	7.0

MedChem Properties

QED Drug-Likeness Score:	0.406	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	5.955	Fsp³:	0.786
MCE-18:	160.16 ? MCE-18 stands for medicinal chemistry evolution.MCE-18≥45 is considered a suitable value.	Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Rejected	GSK Rule:	Accepted
Golden Triangle Rule:	Rejected	BMS Rule:	0
Chelating Alert:	0	PAINS Alert:	0
Colloidal aggregators:	0.217	Fluc inhibitor:	0.041 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.012 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.084 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.281	Promiscuous compounds:	0.508

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.197	MDCK Permeability:	-4.855
Pgp-inhibitor:	0.001	Pgp-substrate:	0.909
PAMPA:	0.994 ? The experimental data for Peff was logarithmically transformed (logPeff). Molecules with log Peff values below 2.0 were classified as low-permeability (Category 0), while those with log Peff values exceeding 2.5 were classified as high-permeability (Category 1).	Human Intestinal Absorption (HIA):	0.016
20% Bioavailability (F20%):	0.672	30% Bioavailability (F30%):	0.409
50% Bioavailability (F50%):	0.978

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.419	MRP1:	0.991
Plasma Protein Binding (PPB):	90.081%	Volume Distribution (VD):	0.102
Fu:	11.702% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.997
OATP1B3 inhibitor:	0.993	BCRP inhibitor:	0.057
BSEP inhibitor:	0.918

ADMET: Metabolism

CYP1A2-inhibitor:	0.999	CYP1A2-substrate:	0.001
CYP2C19-inhibitor:	1.0	CYP2C19-substrate:	0.0
CYP2C9-inhibitor:	0.958	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.054	CYP2D6-substrate:	0.0
CYP3A4-inhibitor:	0.081	CYP3A4-substrate:	0.397
CYP2B6-substrate:	0.001	CYP2C8-inhibitor:	0.987
HLM stability:	0.867 ? Human liver microsomal (HLM) stability. Category 0: stable+ (HLM > 30 min); Category 1: unstable- (HLM ≤ 30 min). The output value is the probability of human liver microsomal instability, where a value closer to 1 indicates a higher likelihood of instability.

ADMET: Excretion

Clearance (CL):

5.076

Half-life (T1/2):

3.051

ADMET: Toxicity

hERG Blockers:	0.036	hERG Blockers (10um):	0.2
Human Hepatotoxicity (H-HT):	0.75	Drug-induced Liver Injury (DILI):	0.128
AMES Toxicity:	0.597	Rat Oral Acute Toxicity:	0.492
Maximum Recommended Daily Dose:	0.69	Skin Sensitization:	0.989
Carcinogencity:	0.909	Eye Corrosion:	0.008
Eye Irritation:	0.515	Respiratory Toxicity:	0.563
Drug-induced Neurotoxicity:	0.171	Ototoxicity:	0.441
Hematotoxicity:	0.206	Drug-induced Nephrotoxicity:	0.806
Genotoxicity:	0.979	RPMI-8226 Immunitoxicity:	0.106
A549 Cytotoxicity:	0.186	Hek293 Cytotoxicity:	0.477
BCF:	0.605 ? Bioconcentration factors are used for considering secondary poisoning potential and assessing risks to human health via the food chain. The unit is -log10[(mg/L)/(1000*MW)].	IGC50:	3.285 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	4.849 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.19 ? 96 hour fathead minnow LC50. The unit of LC50FM is -log10[(mg/L)/(1000*MW)].

Species Source

Organism ID	Organism Name	Taxonomy Level	Family	SuperKingdom	Isolation Part	Collection Location	Collection Time	Reference
NPO28734	Physalis peruviana	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[28617598]
NPO28734	Physalis peruviana	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[30649869]
NPO28734	Physalis peruviana	Species	Solanaceae	Eukaryota	Whole Fruits	n.a.	n.a.	PMID[32159343]
NPO28734	Physalis peruviana	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO28734	Physalis peruviana	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO28734	Physalis peruviana	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]

Note for Reference:
In addition to directly collecting NP source organism data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated them from below databases:
☉ UNPD: Universal Natural Products Database [PMID: 23638153].
☉ StreptomeDB: a database of streptomycetes natural products [PMID: 33051671].
☉ TM-MC: a database of medicinal materials and chemical compounds in Northeast Asian traditional medicine [PMID: 26156871].
☉ TCM@Taiwan: a Traditional Chinese Medicine database [PMID: 21253603].
☉ TCMID: a Traditional Chinese Medicine database [PMID: 29106634].
☉ TCMSP: The traditional Chinese medicine systems pharmacology database and analysis platform [PMID: 24735618].
☉ HerDing: a herb recommendation system to treat diseases using genes and chemicals [PMID: 26980517].
☉ MetaboLights: a metabolomics database [PMID: 27010336].
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

NP Quantity Composition/Concentration

Organism ID	Organism Name	Organism Material Preparation	Organism Part	NP Quantity (Standard)	NP Quantity (Minimum)	NP Quantity (Maximum)	Quantity Unit	Reference

Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP quantitative records for specific NP domains (e.g., NPS from foods or herbs) from domain-specific databases. These databases include:
☉ DUKE: Dr. Duke's Phytochemical and Ethnobotanical Databases.
☉ PHENOL EXPLORER: is the first comprehensive database on polyphenol content in foods [PMID: 24103452], its homepage can be accessed at here.
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

Biological Activity

Activity Type	# Activity
Inhibition	1
IC50	13
GI50	5
Ratio IC50	1
EC50	3

Activity Type	# Activity
Individual protein	6
Cell line	13
Unchecked	1
Non-molecular	1
Others	2

Molecular-level activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT2601	Individual protein	NF-kappaB inhibitor alpha	Homo sapiens	Inhibition	=	46.8	%	PMID[24900739]
NPT2601	Individual protein	NF-kappaB inhibitor alpha	Homo sapiens	IC50	=	18000.0	nM	PMID[24900739]
NPT2816	Individual protein	Bromodomain-containing protein 4	Homo sapiens	IC50	=	1523.0	nM	PMID[36577036]
NPT2816	Individual protein	Bromodomain-containing protein 4	Homo sapiens	IC50	=	556.2	nM	PMID[36577036]
NPT3899	Individual protein	Bromodomain-containing protein 3	Homo sapiens	IC50	=	720.3	nM	PMID[36577036]
NPT3899	Individual protein	Bromodomain-containing protein 3	Homo sapiens	IC50	=	2949.0	nM	PMID[36577036]

In vitro activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT134	Cell line	SK-BR-3	Homo sapiens	GI50	=	710.0	nM	PMID[20438092]
NPT82	Cell line	MDA-MB-231	Homo sapiens	GI50	=	240.0	nM	PMID[20438092]
NPT83	Cell line	MCF7	Homo sapiens	GI50	=	310.0	nM	PMID[20438092]
NPT396	Cell line	T47D	Homo sapiens	GI50	=	160.0	nM	PMID[20438092]
NPT369	Cell line	ACHN	Homo sapiens	IC50	=	489.0	nM	PMID[28257574]
NPT858	Cell line	LNCaP	Homo sapiens	IC50	=	60.0	nM	PMID[28617598]
NPT1629	Cell line	CWR22R	Homo sapiens	IC50	=	70.0	nM	PMID[28617598]
NPT369	Cell line	ACHN	Homo sapiens	IC50	=	460.0	nM	PMID[28617598]
NPT387	Cell line	M14	Homo sapiens	IC50	>	2000.0	nM	PMID[28617598]
NPT170	Cell line	SK-MEL-28	Homo sapiens	IC50	>	2000.0	nM	PMID[28617598]
NPT859	Cell line	HFF	Homo sapiens	IC50	>	2000.0	nM	PMID[28617598]
NPT858	Cell line	LNCaP	Homo sapiens	EC50	=	60.0	nM	PMID[36577036]
NPT859	Cell line	HFF	Homo sapiens	EC50	>	10000.0	nM	PMID[36577036]
NPT28438	Unchecked	Unchecked	n.a.	EC50	=	70.0	nM	PMID[36577036]
NPT20529	Non-molecular	NON-PROTEIN TARGET	n.a.	GI50	=	420.0	nM	PMID[20438092]
NPT2	Others	Unspecified	n.a.	Ratio IC50	=	10.0	n.a.	PMID[24900739]
NPT2	Others	Unspecified	n.a.	IC50	=	980.0	nM	PMID[24900739]

In vivo activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference

Experimental ADME

Experiment Model	Experiment Tissue	ADME Type	ADME Relation	ADME Value	ADME Unit	Reference

Experimental Toxicity

Quantitative toxicity

Experiment Model	Experiment Organism	Toxicity Type	Toxicity Relation	Toxicity Value	Toxicity Unit	Reference

Common Abbreviations:
LC: Lethal Concentration; LD: Lethal Dose; LT:Lethal Time; NOAEL: No-observed-adverse-effect Level; BMDL: Benchmark Dose Lower Confidence Limit; BMD: Benchmark Dose; BMC:Benchmark Concentration; LOAEL: Lowest Observed Adverse Effect Level; RfD:Reference Dose; RfC:Reference Concentration; MRL: Minimal Risk Level; MEG: Maximum Exposure Guideline; PAC: Protective Action Criteria

Categorical toxicity labels

Hepatotoxicity	Carcinogenicity	Mutagenicity	Cardiotoxicity	Respiratory Toxicity	Eye Irritation	Endocrine Disruption

Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP toxicity records from domain-specific databases. These databases include:
☉ ToxValDB: a curated database that compiles quantitative toxicity values for chemicals from diverse public sources to support toxicological research and risk assessment.
☉ TOXRIC: a comprehensive, free-to-access, online database providing toxicological/feature data. The toxicity labels are retrieved from this database. [PMID: 36400569]

Chemically structural similarity

Similar Active Natural Products in NPASS

Top-200 similar NPs were calculated against the active-NP-set (includes approximately 50,000 NPs with experimentally-derived bioactivity available in NPASS)

Similarity is measured using the Tanimoto coefficient (Tc) , which compares the binary fingerprints of two molecules. Tc is calculated as the intersection divided by the union of '1' bits in the fingerprints, ranging from 0 to 1, with 1 indicating highest similarity.

● The left chart: Distribution of similarity level between NPC158285 and all remaining natural products in the NPASS database.
● The right table: Most similar natural products (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	16487
0.1-0.2	27982
0.2-0.3	5168
0.3-0.4	131
0.4-0.5	55
0.5-0.6	17
0.6-0.7	9
0.7-0.8	0
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.7917	Intermediate Similarity	NPC55621
0.7714	Intermediate Similarity	NPC484741
0.7571	Intermediate Similarity	NPC125794
0.7571	Intermediate Similarity	NPC171401
0.75	Intermediate Similarity	NPC484744
0.7465	Intermediate Similarity	NPC285729
0.726	Intermediate Similarity	NPC484745
0.7013	Intermediate Similarity	NPC484719
0.6711	Remote Similarity	NPC484736
0.6494	Remote Similarity	NPC484714
0.6447	Remote Similarity	NPC5073
0.6364	Remote Similarity	NPC484712
0.6216	Remote Similarity	NPC153440
0.6133	Remote Similarity	NPC484742
0.6076	Remote Similarity	NPC166213
0.6076	Remote Similarity	NPC605398
0.6026	Remote Similarity	NPC329671
0.5926	Remote Similarity	NPC164523
0.5921	Remote Similarity	NPC225826
0.5556	Remote Similarity	NPC484692
0.5513	Remote Similarity	NPC270850
0.5513	Remote Similarity	NPC305260
0.5488	Remote Similarity	NPC601815
0.5488	Remote Similarity	NPC607008
0.5443	Remote Similarity	NPC107493
0.5443	Remote Similarity	NPC484743
0.5375	Remote Similarity	NPC103045
0.5294	Remote Similarity	NPC204812
0.5287	Remote Similarity	NPC32868
0.525	Remote Similarity	NPC122056
0.525	Remote Similarity	NPC79579
0.5181	Remote Similarity	NPC287423
0.5176	Remote Similarity	NPC241456
0.5122	Remote Similarity	NPC473203

Similar Clinical/Approved Drugs

Similarity level is defined by Tanimoto coefficient (Tc) between two molecules.

● The left chart: Distribution of similarity level between NPC158285 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	6523
0.1-0.2	2419
0.2-0.3	207
0.3-0.4	1
0.4-0.5	0
0.5-0.6	0
0.6-0.7	0
0.7-0.8	0
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
		NPD

Bioactivity similarity

Similar Natural Products in NPASS

Similarity level is defined by Bioactivity similarity was calculated based on bioactivity descriptors of compounds. The bioactivity descriptors were calculated by a recently developed AI algorithm Chemical Checker (CC) [Nature Biotechnology, 38:1087–1096, 2020; Nature Communications, 12:3932, 2021], which evaluated bioactivity similarities at five levels:
☉ A: chemistry similarity;
☉ B: biological targets similarity;
☉ C: networks similarity;
☉ D: cell-based bioactivity similarity;
☉ E: similarity based on clinical data.
Those 5 categories of CC bioactivity descriptors were calculated and then subjected to manifold projection using UMAP algorithm, to project all NPs on a 2-Dimensional space. The current NP was highlighted with a small circle in the 2-D map. Below figures: left-to-right, A-to-E.

A: chemistry similarity

B: biological targets similarity

C: networks similarity

D: cell-based bioactivity similarity

E: similarity based on clinical data